In the history of intercultural relationships, no country has exercised so great an influence on the English geographical imagination as Russia. From its humble beginnings as the kingdom of Muscovy, to the sprawling expanse of the U.S.S.R., Winston Chruchill’s famous “riddle, wrapped in a mystery, inside an enigma” both captivated and repulsed English audiences. Cartographically split between Europe and Asia, the ambiguous nature of Russian culture not only undermined absolute “Orientalist” binaries separating East from West, but also contributed, through the epoch-making fin de siècle influx of Slavic aesthetic forms, to the birth of English modernism. The idea of “Russianess,” for pre-war audiences, proved crucial to unsettling received notions of art, ideology, and identity. This destabilizing effect is especially evident in the work of Wyndham Lewis, T.S. Eliot, and D.H. Lawrence. Despite having largely been dismissed as “reactionary” and “xenophobic” in their political stances, the complex and variegated way in which each author engages with Russia, as this study demonstrates, suggests an underlying ambivalence in their writing. Rather than reflecting a geographic reality, Slavic society, in their hands, appears as a collective fantasy, an external manifestation of their own internal doubts, anxieties, and pre-occupations concerning “Englishness,” which serves to elucidate the conflicted and uncertain politics of twentieth-century avant-garde art.